Identification
- Name
- Cefdinir
- Accession Number
- DB00535 (APRD00644)
- Type
- Small Molecule
- Groups
- Approved
- Description
Cefdinir (marketed by Abbott Laboratories under the brand name Omnicef) is a semi-synthetic, broad-spectrum antibiotic in the third generation of the cephalosporin class, proven effective for common bacterial infections of the ear, sinus, throat, and skin. It was approved by the U.S. Food and Drug Administration (FDA) in December of 1997.
- Structure
- Synonyms
- (6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Cefdinir
- Cefdinirum
- CFDN
- External IDs
- BMY-28488 / CI 983 / CI-983 / FK 482 / FK-482
- Product Ingredients
Ingredient UNII CAS InChI Key Cefdinir monohydrate 6E7SN358SE 213978-34-8 QWUVJQSNISEEQI-KYIYMPJCSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Omnicef Powder, for suspension 250 mg/5mL Oral Abbvie 1997-12-04 2011-05-31 US Omnicef Capsule 300 mg/1 Oral Abbvie 1997-12-04 2011-05-31 US Omnicef Powder, for suspension 250 mg/5mL Oral Physicians Total Care, Inc. 1997-12-04 2012-06-30 US Omnicef Powder, for suspension 125 mg/5mL Oral Abbvie 1997-12-04 2011-05-31 US - Generic Prescription Products
- International/Other Brands
- Cednir (Abbott) / Cefdiel (Ranbaxy) / Cefzon (Astellas) / Duocef (Ranbaxy) / Efdinir (Incepta) / Idinir (Invision) / Kefnir (Glenmark) / Nirocef (Sel-J) / Oceph (Zuventus) / Omicef (Sel-J) / Omnicef (Abbott Laboratories) / Omnicef R (Janssen) / Palacef (Renata) / Palcef (Renata) / Rtist (Lupin) / Samnir (Siam Bheasach) / Xi Fu Ni (Central Pharm) / Zefdinir (Zydus) / Zinir (FDC)
- Categories
- UNII
- CI0FAO63WC
- CAS number
- 91832-40-5
- Weight
- Average: 395.414
Monoisotopic: 395.035809931 - Chemical Formula
- C14H13N5O5S2
- InChI Key
- RTXOFQZKPXMALH-GHXIOONMSA-N
- InChI
- InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
- IUPAC Name
- (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O
Pharmacology
- Indication
For the treatment of the respiratory, skin, soft tissue, and ENT infections caused by H. influenzae (including b-lactamase producing strains), H. parainfluenzae (including b-lactamase producing strains), S. pneumoniae (penicillin-susceptible strains), S. pyogenes, S. aureus (including b-lactamase producing strains), and M. catarrhalis.
- Associated Conditions
- Acute Exacerbation of Chronic Bronchitis caused by Haemophilus Influenza
- Acute Exacerbation of Chronic Bronchitis caused by Streptococcus Pneumoniae
- Acute Exacerbation of Chronic Bronchitis caused by haemophilus parainfluenza
- Acute exacerbation of chronic bronchitis caused by Moraxella catarrhalis
- Acute maxillary sinusitis caused by H. influenzae
- Acute maxillary sinusitis caused by M. catarrhalis
- Acute maxillary sinusitis caused by penicillin susceptable S.pneumoniae
- Pneumonia due to Haemophilus influenzae (H. influenzae)
- Skin infection caused by S. pyogenes
- Skin infection caused by Staphylococcus aureus
- Streptococcal Pharyngitis
- Streptococcal tonsillitis
- Acute otitis media caused by M. catarrhalis
- Acute otitis media caused by S.pneumoniae
- Bacterial otitis media caused by Haemophilus influenzae
- Community aquired pneumonia caused by H. parainfluenzae
- Community aquired pneumonia caused by M.catarrhalis
- Community aquired pneumonia caused by penicillin susceptable S. pneumoniae
- Pharmacodynamics
Cefdinir is a third generation cephalosporin with a broad spectrum of activity against enteric gram-negative rods. Cefdinir is stable in the presence of some, but not all, b-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins are susceptible to cefdinir. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal.
- Mechanism of action
As with other cephalosporins, bactericidal activity of cefdinir results from inhibition of cell wall synthesis by acting on penicillin binding proteins (PBPs).
Target Actions Organism APenicillin-binding protein 2 inhibitorNeisseria gonorrhoeae APBP3 inhibitorHaemophilus influenzae NMyeloperoxidase inhibitorHumans - Absorption
Maximal plasma cefdinir concentrations occur 2 to 4 hours postdose following capsule or suspension administration. Estimated bioavailability of cefdinir capsules is 21% following administration of a 300 mg capsule dose, and 16% following administration of a 600 mg capsule dose. Estimated absolute bioavailability of cefdinir suspension is 25%. Absorption is reduced by approximately 15% when administered with a high fat meal.
- Volume of distribution
- 0.35±0.29 L/kg [adult subjects]
- 0.67±0.38 L/kg [pediatric subjects (age 6 months to 12 years)]
- Protein binding
60%-70%, binding is independent of concentration.
- Metabolism
Cefdinir is not appreciably metabolized. Activity is primarily due to parent drug.
- Route of elimination
Cefdinir is not appreciably metabolized. Cefdinir is eliminated principally via renal excretion with a mean plasma elimination half-life (t½) of 1.7 (±0.6) hours.
- Half life
1.7 ± 0.6 hours
- Clearance
- renal cl=2 +/- 1 mL/min/kg [healthy]
- Toxicity
Information on cefdinir overdosage in humans is not available. In acute rodent toxicity studies, a single oral 5600-mg/kg dose produced no adverse effects. Toxic signs and symptoms following overdosage with other b-lactam antibiotics have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.
- Affected organisms
- Enteric gram-negative rods
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The risk or severity of bleeding can be increased when Cefdinir is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding can be increased when Cefdinir is combined with (S)-Warfarin. 4-hydroxycoumarin The risk or severity of bleeding can be increased when Cefdinir is combined with 4-hydroxycoumarin. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefdinir. Acenocoumarol The risk or severity of bleeding can be increased when Cefdinir is combined with Acenocoumarol. Acetaminophen The excretion of Cefdinir can be decreased when combined with Acetaminophen. Acetazolamide The excretion of Cefdinir can be decreased when combined with Acetazolamide. Acetylsalicylic acid The excretion of Cefdinir can be decreased when combined with Acetylsalicylic acid. Acyclovir The excretion of Acyclovir can be decreased when combined with Cefdinir. Adefovir Dipivoxil The excretion of Cefdinir can be decreased when combined with Adefovir Dipivoxil. - Food Interactions
- Avoid taking antacids at same time (up to 2 hours before or after antibiotic).
- Avoid taking iron preparations at same time (up to 2 hours before or after antibiotic).
- Take without regard to meals.
References
- Synthesis Reference
Gwan Sun Lee, Young Kil Chang, Jong Pil Chun, Joon Hyung Koh, "Process for preparation of cefdinir." U.S. Patent US6093814, issued December, 1995.
US6093814- General References
- Yamanaka H, Shimazaki J, Imai K, Sugiyama Y, Shida K: Effect of estrogen administration on activities of testosterone 5alpha-reductase, alkaline phosphatase and arginase in the ventral and the dorsolateral prostates of rats. Endocrinol Jpn. 1975 Aug;22(4):297-302. [PubMed:1201739]
- External Links
- Human Metabolome Database
- HMDB0014675
- KEGG Drug
- D00917
- KEGG Compound
- C08110
- PubChem Compound
- 6915944
- PubChem Substance
- 46505573
- ChemSpider
- 5291705
- ChEBI
- 3485
- ChEMBL
- CHEMBL927
- Therapeutic Targets Database
- DAP000436
- PharmGKB
- PA164768739
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Cefdinir
- ATC Codes
- J01DD15 — Cefdinir
- FDA label
- Download (69.2 KB)
- MSDS
- Download (57 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Recruiting Treatment Osteomyelitis 1 1 Completed Not Available Healthy Volunteers 2 1 Completed Treatment Healthy Volunteers 4 2, 3 Completed Treatment Acute Otitis Media 1 2, 3 Recruiting Treatment Mastitis Acute Female 1 4 Completed Not Available Healthy Volunteers 3 4 Completed Treatment Acute Bacterial Sinusitis (ABS) 2 4 Completed Treatment Acute Otitis Media 2 4 Completed Treatment Mild to Moderate Uncomplicated Skin and Skin Structure Infections 1 4 Recruiting Treatment Acute Exacerbation of Chronic Bronchitis (AECB) / Community-Acquired Pneumoniae 1 4 Recruiting Treatment Antibiotics / Pituitary Adenomas 1 4 Recruiting Treatment Pneumonia 1 Not Available Completed Treatment Kwashiorkor / Marasmus 1 Not Available Completed Treatment Snoring / Strep Throat 1
Pharmacoeconomics
- Manufacturers
- Aurobindo pharma ltd
- Lupin ltd
- Orchid healthcare
- Sandoz inc
- Teva pharmaceuticals usa
- Abbott laboratories
- Packagers
- Abbott Laboratories Ltd.
- A-S Medication Solutions LLC
- Aurobindo Pharma Ltd.
- Ceph International Corp.
- DAVA Pharmaceuticals
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Greenstone LLC
- Lupin Pharmaceuticals Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Northstar Rx LLC
- Orchid Healthcare
- PD-Rx Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Redpharm Drug
- Resource Optimization and Innovation LLC
- Sandoz
- Southwood Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- Dosage forms
Form Route Strength Capsule Oral 300 mg/1 Powder, for suspension Oral 125 mg/5mL Powder, for suspension Oral 250 mg/5mL - Prices
Unit description Cost Unit Omnicef 125 mg/5ml Suspension 100ml Bottle 101.59USD bottle Cefdinir 125 mg/5ml Suspension 60ml Bottle 53.05USD bottle Omnicef 300 mg capsule 6.31USD capsule Omnicef 300 mg omni-pac capsule 5.72USD capsule Cefdinir 300 mg capsule 5.22USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US4935507 No 1990-06-19 2011-12-04 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -0.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0878 mg/mL ALOGPS logP 0.02 ALOGPS logP -1.7 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 1.74 ChemAxon pKa (Strongest Basic) 7.45 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 158.21 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 94.34 m3·mol-1 ChemAxon Polarizability 36.12 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption - 0.7692 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.7205 P-glycoprotein substrate Non-substrate 0.5185 P-glycoprotein inhibitor I Non-inhibitor 0.9298 P-glycoprotein inhibitor II Non-inhibitor 0.9165 Renal organic cation transporter Non-inhibitor 0.8919 CYP450 2C9 substrate Non-substrate 0.8676 CYP450 2D6 substrate Non-substrate 0.8203 CYP450 3A4 substrate Non-substrate 0.5821 CYP450 1A2 substrate Non-inhibitor 0.7603 CYP450 2C9 inhibitor Non-inhibitor 0.8303 CYP450 2D6 inhibitor Non-inhibitor 0.894 CYP450 2C19 inhibitor Non-inhibitor 0.8044 CYP450 3A4 inhibitor Non-inhibitor 0.8436 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.953 Ames test Non AMES toxic 0.6686 Carcinogenicity Non-carcinogens 0.8339 Biodegradation Not ready biodegradable 0.9925 Rat acute toxicity 1.8801 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9878 hERG inhibition (predictor II) Non-inhibitor 0.8964
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-004i-2983000000-72bf1ac3398fbaa1531b
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Ketoximes / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines show 10 more
- Substituents
- Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / 2,4-disubstituted 1,3-thiazole / Meta-thiazine / 1,3-thiazol-2-amine / Azole / Ketoxime / Tertiary carboxylic acid amide / Thiazole show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, ketoxime (CHEBI:3485)
Targets
- Kind
- Protein
- Organism
- Neisseria gonorrhoeae
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Penicillin binding
- Specific Function
- Synthesis of cross-linked peptidoglycan from the lipid intermediates.
- Gene Name
- penA
- Uniprot ID
- P08149
- Uniprot Name
- Penicillin-binding protein 2
- Molecular Weight
- 63649.54 Da
References
- Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. [PubMed:17540669]
- Kind
- Protein
- Organism
- Haemophilus influenzae
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Penicillin binding
- Specific Function
- Not Available
- Gene Name
- pbp3
- Uniprot ID
- Q60FT7
- Uniprot Name
- PBP3
- Molecular Weight
- 67295.025 Da
References
- Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. [PubMed:16801430]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Peroxidase activity
- Specific Function
- Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
- Gene Name
- MPO
- Uniprot ID
- P05164
- Uniprot Name
- Myeloperoxidase
- Molecular Weight
- 83867.71 Da
References
- Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [PubMed:8133056]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716]
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
- Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716]
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- Curator comments
- Substrate profile was suggested in vitro using HEK293 cells.
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Substrate and inhibitor profile was demonstrated in vitro using human OAT3 expressed on HEK293 cells.
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]
Drug created on June 13, 2005 07:24 / Updated on December 16, 2018 06:40